Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!
 

The Best Offers
Reduced rates, dining credits and FREE breakfast, spa savings and more

  • Book by 1/20/20
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

    • Princess Tower City Side

    3 nights with flight from $542+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • Aston Waikiki Beach Hotel
    Aston Waikiki Beach Hotel
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    From its urban-Hawaiian beach theme to its vibrant tropical colors and unique decor, this hotel across from Waikiki Beach is fun and full of life.

    • Partial Ocean View King

    3 nights with flight from $566+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • OHANA Waikiki East by Outrigger
    OHANA Waikiki East by Outrigger
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Discover the exceptional value of every stay at OHANA Waikiki East by Outrigger, set in the midst of the city's dynamic cultural scene, just five minutes from the beach and within walking distance of virtually every conceivable type of activity.

    • Waikiki View Two Doubles

    3 nights with flight from $616+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

    • Resort View

    3 nights with flight from $648+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • Sheraton Waikiki
    Sheraton Waikiki
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Located on the best stretch of Waikiki beach, this trendy, sophisticated resort ushers in a new level of style to the Waikiki scene.

    • Standard

    3 nights with flight from $686+

    Los Angeles, California (LAX) departures, valid for travel 12/09/19 - 12/12/19
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  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    • Historic Banyan
    • 15% spa discount
    • Daily Beach Club access for up to two people per room

    3 nights with flight from $732+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This legendary hotel, known as the Pink Palace of the Pacific, offers a redefined luxury experience.
    • Historic
    • 15% spa discount
    • Daily breakfast for two (for 2019 travel only)

    3 nights with flight from $816+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • Embassy Suites - Waikiki Beach Walk
    Embassy Suites - Waikiki Beach Walk
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This all-suite resort, just a short walk from Waikiki Beach, offers spacious and comfortable accommodations.
    • Standard One Bedroom Suite King
    • Complimentary full breakfast daily
    • Nightly two hour cocktail reception

    3 nights with flight from $822+

    San Diego, California (SAN) departures, valid for travel 12/02/19 - 12/05/19
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  • Aston Waikiki Beach Hotel
    Aston Waikiki Beach Hotel
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    From its urban-Hawaiian beach theme to its vibrant tropical colors and unique decor, this hotel across from Waikiki Beach is fun and full of life.

    • Partial Ocean View King

    3 nights with flight from $963+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

    • Historic Banyan
    • 15% spa discount
    • Daily Beach Club access for up to two people per room

    3 nights with flight from $1127+

    Boston, MA (BOS) departures, valid for travel 12/02/19 - 12/05/19
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Hawaii - The Best Offers: Valid on new bookings made 10/28/19 - 01/20/20. Offers vary by hotel and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Blackout dates may apply.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]